The Mid-Career Solopreneur Myth That's Holding You Back

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In this episode, Will Simpson gets honest about the moment he realized he didn’t want a boss. He breaks down the identity crisis that hit after leaving decades of COO/CTO life, the surprising advantage founders over 40 actually have, why solopreneurs must unlearn corporate thinking, and how embracing “good enough” is the key to launching anything.

If you’ve ever wondered whether you’re too late, too structured, too corporate, or too unsure to build something of your own…this conversation is the permission slip you’ve been waiting for.

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Connect with Will Simpson

• Connect on LinkedIn

• Visit PivotReady
• Email will@pivotready.co

Favorite Quote About Success:

"I grinded for five years and was an overnight success."

Episode FAQs

What makes this episode valuable for solopreneurs who come from the corporate world?

Will explains exactly why corporate experience does translate, just not in the ways you think. He talks through the mindset traps, the “ambient stress” you leave behind, and how to rewire yourself for small-ball thinking, fast execution, and building something that actually energizes you.

Does Will think it’s harder to become a founder after 40?

Not at all, he argues the opposite. According to Will, founders over 40 bring unmatched domain expertise, resilience, and clarity. The data supports it, and he shares why experience gives mid-career professionals an overlooked edge that younger founders simply can’t replicate.

What’s Will’s top advice for solopreneurs who want to use AI or no-code tools?

He stresses that AI can help you build prototypes fast, but not without structure, constraints, and actual expertise guiding it. He breaks down why you can’t “speak” a fully functional app into existence, how to think like a builder instead of a coder, and why you should ship an MVP that’s slightly embarrassing.

Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr Intro gives you free education, community, and tools to build a thriving one-person business. 

So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, click here to check out LifeStarr Intro!  

About Will Simpson

Will Simpson is not your typical C-Suite veteran, though he’s spent decades leading technology, operations, and engineering at the highest levels. His story is really one of reinvention.

• Version one: a pool-hall hustler and poker player in 1980s and ’90s Austin.
• Version two: a single father who launched a successful career in tech and executive leadership.
• Version three: the pursuit of joy—marrying his best friend on 7/11 (Slurpee® Day, of course) and discovering a love for storytelling. He published his first novel in 2023, with the next already underway.

That creative leap sparked version four: entrepreneurship. After realizing the “hustler” in his own fiction was really an entrepreneur in disguise, Will embraced that identity himself, co-founding two companies in just nine months.

Influential? Innovative? Sure. But more importantly, he’s a builder, a storyteller, and a man who’s rewriting his life one version at a time.